


little red riding hood (and the big bad wolf)

by poetictragedy



Category: Teen Wolf (TV)
Genre: Biting, Cunnilingus, F/M, Fingerfucking, First Time, Girl!Stiles, Hair Pulling, Halloween, Nipple Play, Underage Drinking
Language: English
Status: Completed
Published: 2013-03-30
Updated: 2013-03-30
Packaged: 2017-12-06 23:04:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,478
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/741205
Author URL: https://archiveofourown.org/users/poetictragedy/pseuds/poetictragedy
Summary: <blockquote class="userstuff">
              <p>It's Halloween and Lydia is, as she always does, throwing a party. Stiles, after being reluctant to go, shows up in an outfit that has everyone surprised and she unintentionally finds the person she's been looking for: the Big Bad Wolf, AKA Jackson.</p><p>Little Red and Big Bad have some fun.</p>
            </blockquote>





	little red riding hood (and the big bad wolf)

**Author's Note:**

> Right, I know that this is completely overdone and I realized that when I was halfway through writing this fic but, whatever, someone's going to enjoy it, right?
> 
> Also, I will have all of you know that I probably got some things wrong because I haven't written hetero sex in a long, long time and I apologize for any mistakes you found (grammar-wise, punctuation-wise, or in the smut scenes; I tried my hardest!). (I do know for a fact that there are a couple of mistakes in here, I just can't remember and don't feel like going through this with a fine toothed comb.)
> 
> (Oh and [this](http://counterculturebeauty.com/wp-content/uploads/2011/10/miss-little-red-riding-hood-costume.jpg) is the dress Stiles is wearing.)

The Jeep slows down in front of the house and Stiles looks at it, chewing on her lower lip before pulling up, swinging the vehicle into a spot behind a familiar silver Porsche. She lets the engine idle for a moment as she thinks about what she’s doing and curses Lydia for begging her to come to her stupid Halloween party.

When Lydia announced that she was having a party, Stiles hadn’t planned on going and she knew that if she did, she wouldn’t dress up. That was three weeks ago and, since then, Lydia has managed to convince her to not only come to the party but to dress up as well.

So that’s why Stiles is currently sitting inside of her Jeep in a too-tight, too-short,  _too-red_  dress. That had been her idea, though, so she can’t blame Lydia for the costume but she sure as hell can blame the werewolf for practically forcing her to come. 

 _Fucking werewolves_ , Stiles thinks as she shuts the engine off and opens the door, shivering a little as a cold breeze kicks up. She should have gone with something else, maybe something with pants, but it’s far too late for her to turn back now.

After climbing out, Stiles grabs her red hoodie and shrugs into it, pulling the hood up over her curls. She shuts the door and bends to look at herself in the mirror, feeling proud of the makeup she applied to her eyes, cheeks, and lips. It’s nothing fancy: just a simple eye shadow (a smoky gray colour), eyeliner (black), blush (a rosy colour), and a smearing of pink lip gloss. 

Stiles straightens up and moves her hands down, playing with the fishnet stockings she had thrown on as an after thought. The woman in the picture online had been wearing thigh-high white socks and Stiles had scoffed, proclaiming she didn’t want those because it looked like something she’d seen in a porn.

The outfit she chose was, of course, Little Red Riding Hood and where the model on the site had heels on, Stiles had Doc Martens. She also got rid of the red caplet that came with it and substituted her red hoodie instead. It made her feel a little more badass and confident, not slutty like she thought she would feel.

“Okay, Little Red, it’s now or never.” Huffing out a sigh, Stiles adjusts the corset and grunts, making sure it’s covering as much of her chest as possible. There’s still cleavage — an impressive amount, in fact — but there’s not much else she can do, so Stiles drops her hands, stuffing them into her hoodie pockets.

Somewhere behind her, someone whistles and she blushes, walking toward Lydia’s house with her heart pounding in her chest. She can smell cigarette smoke and beer as soon as she gets to the door, the combination of smells doing nothing to relax her.

Stiles hesitates at the door for a moment before going inside, walking around until she runs — literally — into Scott, who’s dressed up like a zombie. It’s a cute outfit, she thinks, and she smiles at him, standing on her tiptoes to pat his head lightly.

When she pulls back, Stiles notices Scott is looking at her and she blinks, her eyes narrowed. “What?”

“Little Red?” Scott asks, incredulous. “ _Seriously_?”

“What’s the matter with Little Red?”

“Nothing,” he answers, shrugging his shoulder as he looks her up and down, a grin spreading across his face. “Derek is going to rip your throat out for wearing that.”

Stiles scoffs and waves a hand dismissively, grinning. “Do I look like I’m scared of the Big Bad Wolf, Scott?” As if that were his cue, Scott opens his mouth, his fangs extending and Stiles shivers a little. “Nope. Nothing,” she hums and pats his cheek before walking away.

When she gets to the kitchen, Stiles immediately goes to the table where dozens of bottles are scattered, humming to the song that’s playing in the other room as she looks at her options. A hand reaches out and grabs the bottle Stiles was going for, causing her to pout and look up at the man who stole her booze.

And it’s Derek — dressed in a cop uniform.

“Oh my god,” she whispers and lifts both hands, covering her mouth before erupting into a giggle fit.

“It was Isaac’s idea,” Derek explains, his eyes going wide as he drags them down Stiles’ body and back up. “Really?”

“Why is everyone looking at me like that? I’m the only human in an all werewolf pack, so I think Little Red is totally acceptable.”

Derek shakes his head and pours more whiskey into his red solo cup, handing the bottle to Stiles when he’s done. “I don’t remember Little Red showing cleavage,” he points out and laughs, looking down at her boots, “or wearing Doc Martens.”

“Little Red can do whatever she pleases.” With a smug smile, Stiles grabs a cup from the tower in the corner of the table and pours a good amount of whiskey into it. “So,” she says before taking a sip, her face scrunching a little, “what’s Isaac dressed as, then?”

“A prisoner. He got an orange jumpsuit somewhere and said it’d be fun if  we dressed up as a cop and a prisoner.”

Stiles grins and bites her lip. “That’s weirdly adorable — in a kinky kind of way,” she says, moving a hand to touch the handcuffs attached to Derek’s belt. “You going to use these on him later, officer?”

“ _Stiles_ ,” Derek growls.

“You gonna handcuff him to the bed so he doesn’t run away?” Stiles bats her eyelashes at Derek and grins up at him, pulling her hand away as she takes another sip of her drink. “I had no idea Isaac was so kinky.”

When Stiles looks up again, Derek’s face is red and the outside of his green irises are rimmed in crimson. She squeaks, biting her lower lip again as she lifts a hand, patting his chest. “Good talk,” she says and smiles before turning on her heels.

Before Derek can say anything else, Stiles moves into the living room, nursing her whiskey as she walks. A few people compliment her outfit and she beams proudly as she thanks them. She walks around and finds Isaac in the corner talking to Allison, who’s dressed in a white tank top and camo pants, fake blood smeared on them.

“Let me guess,” Stiles says as she comes closer, standing between her friends, grinning, “you’re a zombie hunter.”

“How’d you know?” Allison asks, grinning so wide that her dimples set deep into her cheeks. Stiles shrugs and mumbles something about Scott around the lip of her cup before draining the rest of her whiskey. “I forgot I let him go for a moment.”

Stiles laughs and shakes her head. “You might want to catch him before he goes off and starts biting people,” she replies, nudging her elbow against Isaac’s and turns to look at him. “By the way — I saw your boyfriend. Hot cop?  _God_ , yes.”

A sheepish smile takes it’s place on Isaac’s face and he looks at her outfit, quirking a brow. “And you’re… Little Red?” Stiles nods her head and beams up at him, lifting a hand to pat his cheek. “It’s a nice outfit but I didn’t expect  _you_  to ever wear it.”

“Why not?” Stiles asks, pouting. “I  _do_  wear dresses, you know!”

“Yeah,” Allison interjects with a laugh, “but they’re usually worn over top of ripped jeans and underneath Scott’s lacrosse hoodie.”

Crimson bleeds into Stiles’ cheeks and she huffs. “I don’t like wearing dresses because when the wind kicks up,  _everyone_  will be able to see my underwear,” she mumbles.

“And jeans are more comfortable.” A laugh escapes Allison’s throat and she leans down to kiss Stiles’ cheek before moving away. “You look good in that costume, though,” she says and excuses herself, yelling Scott’s name as she walks away.

Stiles shakes her head and turns to Isaac, smiling. “So, puppy, tell me the truth: you suggested the cop/prisoner thing because you’ve secretly always wanted to see Derek in a cop uniform,” she accuses. “Right?”

“Don’t tell him that but…. yes.” Isaac gives her a lopsided grin and leans down to hug her, pulling away as he looks up. “Speaking of…” he trails off, making a vague motion in the corner, where Derek is standing, twirling a billy club.

“Yeah, yeah, go. Go make out with the hot cop.” Laughing, Stiles gives Isaac a playful shove and watches him walk away, shaking her head. Once alone, she looks down into her cup and frowns, turning to go back into the kitchen, squeezing between two couples that are dancing dangerously close together.

The kitchen is packed with people and Stiles has to elbow her way through the crowd to get back to the table, huffing once she does. She lets out a yelp when someone pushes her into the edge of the table and glares at the back of the guy’s head.  _Asshole_ , Stiles thinks as she turns back, sighing.

“That’s mine,” a deep voice says as he takes the bottle of Jack Daniels away from Stiles, dumping an impressive amount into his cup. Stiles turns to glare at him and blinks, coming face-to-face with a tall boy in a wolf mask. “Little Red,” he says and the way he talks tells Stiles he’s grinning.

Humming, Stiles nods and takes the bottle away with a smile. “Why, is that the Big Bad Wolf?  _Oh no_ ,” she says, feigning fright as she pours more whiskey into her cup, setting the bottle down. She grabs a can of Coke, cracks it open, and pours a generous amount into the whiskey.

“You’d be afraid if you knew who was underneath this mask.” The voice sounds familiar but Stiles can’t place a name to it. She just hums and shakes her head, the hood of her jacket coming off. “Anyone tell you that you look sexy in that?”

“No, you’re the first,” Stiles answers, looking up at the boy with a bright smile, lifting a hand to touch the nose on his mask. “I’d like to say the same about you but, you know, wolves and girls? That’s illegal.”

A laugh comes from behind the mask and Stiles’ heart skips quite a few beats when she hears it. “You want to see what’s under the mask, Red?”

“Oh, no, I don’t want that; you might eat me.”

“Well…” The voice trails off and Stiles’ eyes go wide, her cheeks turning a deeper shade of crimson when she realizes what she said. “You know who I am, Stiles,” he says and lifts a hand to touch her curls before brushing the pad of his thumb along her jaw.

Scrunching her nose, Stiles licks her lips and tries to focus on anything but the way her heart is hammering behind her ribs. She shakes her head and gives the boy an  _‘I don’t know who you are’_ expression before taking a long sip from her cup. That calms her down for a second, until the boy laughs again and she swallows.

“Think about it and come find me.” With that, the boy walks away, his hand brushing along the back of Stiles’ before disappearing. A shudder passes through her when she feels that and she takes a deep breath as she goes back into the living room.

The first person she finds is Derek and she pulls him off to the side, huffing as she collects her thoughts. When she does, Stiles opens her mouth to ask, “Who’s in the wolf mask?”

“The — _what_?” Derek asks, his eyebrows pulling together.

“Come on, you’re not an idiot. There’s a boy walking around here in a wolf mask and I want you to tell me who it is,” she replies, licking her lips quickly as she thinks about the voice she heard.

Derek lifts an eyebrow and smirks. “You really want to know?”

“Yes, goddamnit, I want to know! Don’t hold out on me, Derek.”

“Jackson was walking around with a wolf mask in his hand earlier and I haven’t seen anyone else in one.” When Derek says that, Stiles blinks at him and laughs loudly, slapping him on the chest before asking who’s really in the mask. “Jackson,” he answers again and grins before moving away to join Isaac.

There was  _no way_  Jackson was the boy in the mask because he had called Stiles sexy and she knew, for a fact, that Jackson didn’t think she was even remotely sexy. Then she thinks about the voice she heard and, god, that laugh that made her tingle in all the right places.

“Holy shit.” The words come out as a whisper and Stiles downs the rest of her Jack and Coke, setting the empty cup down on the first flat surface she can find. She chews on the edge of her lip and walks around the room, standing on her tiptoes and straining her neck to look around, frowning when she doesn’t see Jackson anywhere.

Just when she’s about to move on and go upstairs, Stiles feels a hand on her shoulder and spins around to look at Lydia, who’s dressed as a very sexy witch. Her cleavage is popping out and it takes all Stiles has in her not to stare at it. Not because she’s attracted to Lydia because, goddamn, how can you  _not_  look?

“Little Red,” Lydia says and hums, grinning slowly. “I should have known.”

Stiles rolls her eyes but smiles, nodding. “Yep. I figured I would be cliche for a night and I figured, you know, you’d approve of me dressing in something  _girly_ ,” she answers.

“Oh, I definitely approve but I have to wonder — who are you wearing it for?”

“Huh?”

“Which wolf,” Lydia explains, her eyes set on Stiles’, the grin still in place.

When Stiles gets it, she blushes and shrugs, licking his lips, completely taking the lip gloss off of them. “None of them? I kind of thought it was ironic and kind of perfect for the only female human in an all wolf pack,” she mumbles.

“Huh.” The grin on Lydia’s face softens and she nods. “I thought maybe you’d wear it for, oh, I dunno — Peter.”

“Peter? Dude,  _no_ , he’s almost my dad’s age!” Stiles shakes her head and shudders, making a face at the thought of being with Peter. Just — no. Ugh.

Lydia nods and smiles, leaning in to whisper, “Good. He’s my Big Bad Wolf — if you get what I’m saying.” 

Oh, Stiles gets what Lydia is saying and wants so badly for them not to have this conversation. She breathes a sigh of relief when Peter comes over, not dressed in a costume but his every day clothes, his arm slipping around Lydia’s waist. A comment rises in Stiles’ throat and she forces it down, letting the words die away.

“Right,” Stiles says, giving Peter a shaky smile before pointing over her shoulder, “I’m going to let you two do… whatever it is you’re going to do and I’m going to find Scott.”

“Scott’s right there,” Peter points out, tipping his head to the corner and Stiles follows his gaze, seeing her best friend standing in the corner with Allison. Making out, of course.

Stiles bites her lip and laughs, looking back at the pair in front of her. “And now that I’ve found him, I’m going to avoid him like the plague until either Allison sucks his face off or he comes up for air,” she says and moves toward the stairs quickly, stumbling up them before either Peter or Lydia can say something.

There are a few people scattered upstairs and Stiles mumbles apologies as she bumps into a few of them on her way to a guest room. She just needs to be alone for a moment to process everything and to get the image of Peter and Lydia out of her mind. Seriously, how could she be with  _that psycho_? It was confusing and Stiles knew that she’d never understand.

Once she finds an empty guest room, Stiles ducks inside and turns the light on, sighing heavily as she makes her way over to the bed. Her boots clack against the floor and she focuses on the noise, finding that it calms her down. So when she sits down, Stiles taps the toe of her boot against the floor and listens to it, her mind wandering.

Jackson Whittemore had actually called her sexy. That was kind of mind blowing and Stiles wonders if Derek was really just fucking with her because Jackson is a thousand leagues away from the one she’s in and… well, Derek’s an asshole.

“But what if he was telling the truth?” Stiles asks herself, pressing her hands between her knees, lacing her fingers together. If Jackson really was the boy in the mask (and, by this point, Stiles is almost ninety-nine-point-nine percent sure he was), then that means he must have an ounce of feeling for her. 

Stiles sucks in a sharp breath and looks at the door, listening to the noise coming up from downstairs as she thinks about how all of her friends are paired off. Scott is with Allison; Derek is head over heels in love with Isaac; Lydia is fawning over Peter; Erica and Boyd are practically attached at the hip; and even Danny has a boyfriend this year.

So why shouldn’t the last two single people in the pack get together? Because, Stiles answers herself, there has to be a mutual attraction between both parties and while she thinks Jackson is the most gorgeous man she’s ever laid eyes on, Stiles isn’t sure he likes her back.

With a frustrated sigh, Stiles flops back against the middle of the bed and stares up at the ceiling, chewing on the edge of her lip. She plays with the hem of her dress, running her fingers along the frilly edge as she tries to think about something that isn’t Jackson.

A few minutes later, the door creaks open and she calls out: “Room’s occupied!”

“Ah, Little Red.” The voice from before fills the room and Stiles presses her thighs together on instinct, biting back a moan. “I was hoping I’d find you again.”

“Well, you caught me,” Stiles says, swallowing thickly as she pushes herself up onto her elbows, looking at the boy standing by the door. “Are you going to eat me now that you’ve found me?”

The boy laughs and shakes his head coming forward. His shoes hit the floor heavily and Stiles shivers, swallowing again. Once he’s standing at the edge of the bed next to her legs, the boy lifts a hand and touches the bottom of her dress. “Is that what you want?”

“Well,” she answers, her voice cracking a little, “you have to take your mask off to do any kind of eating.”

“Have you figured out who I am yet?”

“Kind of but I had a little help.” No response comes and Stiles blushes when she realizes that he’s waiting for her to answer. “Derek told me you —  _Jackson_  — were walking around, carrying a wolf mask earlier.”

A deep chuckle fills the room and Stiles shudders, watching as a hand lifts up to pull the mask off, revealing a grinning Jackson underneath. “I figured Hale would sell me out,” he mumbles.

“I forced it out of him,” Stiles replies and smiles, her stomach flipping as she looks up at Jackson, heart pounding hard. “Why didn’t you just tell me who you were in the first place?”

“Because this was more fun.” Tossing the mask onto the bed beside Stiles, Jackson moves one of his hands down to run along the outside of her thigh. “And I wanted to keep the Big bad Wolf act up for a little longer.”

Stiles laughs and bites her lip, letting her eyes flutter shut. “Asshole,” she murmurs.

“Hey, is that any way to treat a vicious wolf?” Jackson moves and puts a hand on either side of Stiles’ head on the mattress, leaning his body over top of hers. “One that could tear your throat out,” he whispers.

“Mmmm..” Blinking her eyes open, Stiles looks at Jackson and gasps when she sees his fangs, heat pooling in the pit of her stomach. “Oh what big teeth you have,” she whispers, lifting a hand to touch the side of his face, smiling. 

Jackson snorts and responds with, “The better to eat you with.”

“Oh sweet fuck.”

“Hmm?”

A blush creeps along Stiles’ cheeks and she shakes her head. “It shouldn’t be this hot,” she answers, moving a hand down to play with the hem of Jackson’s t-shirt. “You pretending to be the Big Bad Wolf and showing me your  _fangs_.”

“Do you want me to put them away?” 

“No,” Stiles answers, quickly, and she blushes harder. “Just… leave them out for a little while longer? It’s hot, you know, the fangs and your general  _everything_ , really.”

Jackson smiles and leans down, ducking his head under Stiles’ chin, kissing across her chest before biting down on her collarbone. Pain and pleasure mix, shooting through Stiles’ core as she arches off the mattress, moving a hand into Jackson’s hair, gripping it tightly.

When the wolf sucks on the bite mark, Stiles gasps and clenches her eyes shut, digging her nails into Jackson’s scalp. “Jesus,” she hisses, spreading her legs and laying one against either side of his body, bracketing him.

“What?” Jackson asks when he pulls back, his lips brushing along Stiles’ skin. “You’re enjoying this; I can smell how turned on you are,” he mumbles.

“God, you could you just — could you  _not_?”

“Could I not… what?” _  
_

Stiles huffs and drags her hands down, gripping the fabric covering Jackson’s body, tugging it up slowly. “Could you not talk about how you can _smell me_?”

“But I can,” Jackson whispers, moving up to press his lips against Stiles’ ear, “and I can smell how  _wet_ you are. You have no idea what that does to me.” 

A whimper escapes and Stiles chews on her lower lip, lifting her hips off the bed to press them against Jackson’s, moaning softly. She doesn’t say anything else, just lets small moans and whimpers escape as she feels his lips against her ear, breath falling soft against the shell.

One of Jackson’s hands slips between them and underneath her dress, his palm pressing against her. He growls in Stiles’ ear and bites at the lobe before dropping down to kiss her neck, biting and sucking on her pulse. 

“Jacks — Jackson,” Stiles gasps, her hips moving against his hand slowly, desperate noises rising from her throat. His grin is all wolf and white fangs, a purr settling low in his throat as he moves his hand up, pressing a fingertip against Stiles’ clit.

When Jackson’s finger moves in a slow circle, it’s like a jolt goes through Stiles’ body and she grips his t-shirt tightly, digging her nails into the fabric. She moves her hips along with his finger and they find an easy rhythm that has Stiles breathless. The only other person that’s touched her like this is herself and she had no idea it could be ten  _thousand_  times more enjoyable and awesome with someone else. 

Especially with said someone is  _Jackson freaking Whittemore._

Pulling away, Jackson moves off the bed and gently tugs Stiles up with him, pushing her hoodie back and off her shoulders, watching the red fabric drag across her pale skin. Once it’s to her elbows, Stiles takes it off and throws it somewhere past the end of the bed, her lip caught between her teeth when she looks up at Jackson.

“It’s okay,” he says and toes out of his shoes, kicking them away before dropping down onto his knees. Jackson undoes Stiles’ boots, pulling them off one at a time and setting them on the floor, his hands going up her legs. “Your heart’s beating like crazy.”

“Well  _no shit_ , Sherlock.” Stiles’ voice is shaky when she responds and she shivers, feeling Jackson’s hands travel up the length of her legs, stopping on her thighs. “You’re, like, the sexiest person I’ve ever seen and your hands are currently on my thighs. So, yeah, my heart is going to beat fast; any girl’s heart would, if they were in my situation.”

A smile tugs at the corners of Jackson’s mouth as he moves his fingers higher, hooking the tips underneath the waistband of Stiles’ fishnet stockings. “Just relax,” he whispers, tugging the stockings down before pulling back, pulling them off Stiles’ legs. Jackson throws them onto the floor and slides his hands right back up her legs, tugging her to the edge of the mattress. “I won’t bite — unless you want me to.”

Stiles sucks in a breath and nods, whispering, “God, yes — bite me.”

“Yeah?” Jackson asks, quirking a brow as he looks up at Stiles, grinning when she nods her head and mumbles a quiet ‘please’ as she moves a hand through his hair. “You know, I  _really do_  think you look sexy in this costume,” he murmurs, moving his hands between Stiles’ thighs spreading them slowly. “Lie back.”

Without hesitating, Stiles lays back on the bed and brings her feet up, pressing her heels against the bed frame, her eyes settled on the ceiling. She breathes in slowly and rolls her lips in over her teeth, fingers shaking as she cards them through Jackson’s hair. 

And even though she knows what’s going to happen, Stiles is nervous. Her thighs are trembling as Jackson spreads them, his hands going up to her hips. She lets out a quiet gasp when she feels her boy shorts pull away from her, the soft cotton dragging across her skin as Jackson pulls them off.

They’re gone a few seconds later, probably thrown somewhere on the floor but Stiles isn’t thinking about that. She’s focusing on the way Jackson’s hands feel against her, his fingers skidding up her thighs, moving up to push her dress up a little. It seems like forever has gone by before Stiles feels lips brushing along the insides of her thighs and she squeaks, instinctively pulling them together.

“Shit,” she breathes, forcing herself to relax, feeling Jackson’s fingers stroking the outside of her thigh, his mouth moving down toward her knee. He presses a kiss to it and Stiles, despite herself, smiles at how affectionate the action is. “I’m okay,” she says, after a moment, and opens her legs again.

Jackson continues stroking her skin as he moves up, mumbling, “I’m not going to hurt you.”

A nervous laugh bubbles up from Stiles’ throat and she goes to open her mouth to say that she  _knows_ he’s not going to, but a surprised squeak escapes instead. She clenches her eyes shut and breathes in deeply, feeling the tip of Jackson’s tongue against her. It’s like nothing she’s felt before and she lifts her hips up against the action, silently begging for more.

Jackson takes a deep breath and spreads Stiles’ legs a little more, putting his hands on the backs of her thighs before tugging her closer. He hooks her legs over his shoulders and moves down to flick his tongue against her slit, lapping at her gently.

“Oh… oh god, Jackson.” 

“ _Hmm_?” Jackson hums as he continues to lick in broader strokes, dragging the flat of his tongue up to her clit. He seals his lips around the sensitive skin and sucks gently, moving one of his hands down, running a fingertip along Stiles’ entrance. Carefully, Jackson slips the fingertip inside and smirks when he hears her moan quietly above him.

Stiles buries both hands into Jackson’s hair and grips tightly. “That… oh, that feels good,” she murmurs, licking her lips and biting down on the lower one, feeling the length of Jackson’s finger slip inside her. “Oh sweet _Jesus._ ”

From where he is, Jackson laughs and continues to suck on her clit, working his finger in and out slowly, the digit moving easily with how wet Stiles is. His mouth is watering and he moves down suddenly, pressing his tongue in right beside his finger, fucking her with both of them.

“Jackson,  _fuck_.” The way Stiles says his name makes Jackson growl and he pulls his tongue out, slipping two fingers inside of her, turning his head to kiss the inside of her thigh. He bites at the pale, smooth flesh, sucking on the mark, determined to leave a hickey. Above him, Stiles moans his name and starts moving her hips against his hand, prompting him to thrust his fingers in a little harder.

Humming again, Jackson kisses his way down Stiles’ thigh, biting just above her knee before pulling back. He keeps his hand where it is, fingers pumping in and out of her a little faster, and moves up to kiss her chest, biting at her breasts. Stiles’ hands move to his shoulders and she digs her nails in, hips rocking against his hand and breathless little moans leaving her throat.

Jackson licks his lips and moves up, ghosting his mouth over Stiles’. “You okay?” 

“I’m —  _ohhh_  — good, yeah,” is Stiles’ answer and Jackson smirks, kissing her hard, licking into her mouth when she parts her lips. She moans into the kiss and moves a hand to the back of his head, fingers tangling in his hair, pulling him closer. When Jackson pulls back, Stiles whines in disappointment, the noise tapering off into a strangled cry when his fingers crook inside of her. “Fuck!”

Another long, drawn out whine escapes when Jackson pulls his fingers out and he kisses her apologetically, pulling her up before easing away. He moves his dry hand around, finding the zipper to Stiles’ dress and tugging it down quickly, licking his lips. Once he has the dress unzipped, Jackson pulls back and undoes his jeans, shoving them down.

Stiles’ eyes go wide when she watches him and she swallows. “Are you — are we really?”

“Do you want to?” Jackson asks in mid-step, his jeans half off and half on. 

“I mean, uh, I thought that was kind of apparent but the fact that I’m about to lose my virginity very soon is kind of hitting me and…  _wow_.” The words come out in a rush and she blushes, pulling her dress off before sipping it down her legs. The red and black fabric falls to the floor and Stiles is left naked in front of Jackson, her teeth worrying over her lip. “I do want this,” she says, finally, and smiles at him. “Really.”

That makes Jackson sigh in relief and he pulls his jeans off, grabbing a condom from the front pocket, putting it between his lips before tossing the denim away. He tugs his shirt up and over his head next, throwing it onto the floor behind him as he looks at Stiles, groaning. Before moving forward, though, Jackson goes to lock the door and makes sure it’s secure, his heart hammering as he moves back to the bed.

“How do you want me?” Stiles asks and she laughs, the sound high pitched and nervous.

Jackson blinks and takes the wrapper out from between his lips, setting it down on the nightstand. “Just lay back on the bed and relax,” he whispers, helping Stiles move so she’s laying the right way. 

Once she’s settled, Stiles rests her hands low on her stomach, turning her head to watch Jackson step out of his boxer briefs, inhaling sharply when she sees his cock. She knew he was big — who  _doesn’t_? — but she wasn’t expecting that and her nerves shoot through the roof. Jackson senses this and he climbs onto the bed, holding himself up above her, smiling as he leans down, peppering Stiles’ face with soft kisses.

“You’ll be okay,” he whispers, nudging his nose against her cheekbone, breathing in deeply. “I promise. If you can’t handle it or want to stop, just let me know.”

“Okay,” Stiles breathes, nodding firmly as she smiles up at Jackson. “I’m ready.”

Jackson licks his lips and nods, leaning down to kiss Stiles before pulling away. He spreads her legs and settles onto his knees between them, reaching over to grab the condom, his fingers shaking slightly. It’s funny, he thinks, because he wasn’t nearly this nervous with Lydia when it had been their first time together. Maybe Jackson was nervous now because he could feel everything Stiles was feeling and that made him want to be extra careful not to hurt her.

Sighing, he tears the top of the wrapper off and takes the condom out, laying the foil on the mattress beside them, giving Stiles a soft smile. He keeps their eyes locked as he expertly slides the latex over his cock, rolling it down until it’s snug at the base. Once it’s secure, Jackson leans down to kiss Stiles slowly, moving his hands along her body slowly, dragging them across her breasts and stomach, brushing his thumb over her clit.

“Come —  _oh_  — on, Jackson..” Stiles pants when she pulls back, giving Jackson a lazy grin. He rolls his eyes and straightens up, taking one of her hands in his own as he wraps the other around the base of his cock. 

After giving Stiles one last, questioning look, Jackson presses the head of his cock against her slit and bites back a moan, feeling how wet she is. He hesitates and only moves when Stiles rolls her hips, biting her lower lip as she encourages him to keep going.

The head of his cock slips inside of her and Stiles whimpers. “Oh, ow,” she gasps, squeezing Jackson’s hand tightly, her eyes screwed shut. “Shit, how — how does anyone like this?”

“The first time always hurts,” Jackson murmurs, bringing their hands up to brush his lips along the back of Stiles’ knuckles, leaving just he head of his cock buried in her. “Tell me when you’re ready and I’ll keep going.”

Stiles nods her head and sucks in a breath, holding it as she forces herself to relax. The pain starts to ebb, turning into a dull aching that she can definitely handle, and she tell Jackson to keep going — but to go slowly. She keeps holding his hand and brings her free one up, clamping it down on her mouth, whimpering behind it. 

Jackson’s cock inches into her and Stiles makes him stop after a few minutes, her hands on his chest and tears rimming her eyes. She knew that it was going to hurt and she knew that it wasn’t going to be all rainbows and sunshine the first time — but she didn’t expect it to hurt so bad. Maybe it’s because she’s a virgin that’s only had three of her own slim fingers inside of her and now she’s trying to take Jackson’s long, thick cock. Or maybe it’s because she isn’t relaxed enough — who knows?

Then there’s a hand on her face, fingers stroking across her cheek, and Stiles tilts into the touch, breathing in slowly. She opens her eyes to look at Jackson, her chest tightening when she sees the concerned look on his face. Taking a deep breath, she moves both of her hands up and cups the sides of his neck, tugging Jackson down until they’re kissing. 

The kiss is slow and Stiles takes charge, moving her lips against Jackson’s, experimentally dragging her tongue along the swell of his lower lip. She smiles when she hears him gasp and it calms her down, untangling the knots in her stomach as they kiss languidly. After a few minutes, though, Stiles feels the heat in her stomach coil tighter and she finds herself moving her hips against Jackson.

“You sure?” He pants as they ease apart and Stiles nods her head, brushing the tips of their noses together, smiling softly. When she lays back, Jackson nods and moves a hand down to his cock again, guiding another inch inside of Stiles, biting his lip. 

Stiles gasps and screws her eyes shut again, the pain turning into a pleasurable burn. She moves her hands down Jackson’s arms, resting them just above his elbows, fingers squeezing his muscles as he continues slipping inside of her.

As soon as he’s all the way in, Jackson gasps and looks down at Stiles, trying to figure out what she’s feeling. He knows that she’s in pain and he can feel it, the weight of it causing his chest to tighten painfully. When Stiles wraps her legs around his waist, Jackson leans down to kiss her chest, biting her breasts gently and leaving red marks in his wake.

“Jackson,” she gasps, rolling her hips with a painful whimper. “Move, baby.”

That name sends a jolt down Jackson’s spine and he shudders, pulling out of Stiles slowly, smoothing his hands down her thighs, comforting her. He drags his cock out halfway and thrusts into her again, going as slow as humanly possible. 

“Fuck, Stiles,” he groans, bottoming out again as he grips her thighs gently. He buries his face against her chest and smiles when he feels her hands in his hair, fingers running through the short locks slowly. 

Stiles adjusts quickly and she starts moving against Jackson, her gasps sounding only a little painful this time. He starts thrusting in a little faster, keeping his movements short and slow as not to hurt Stiles, and moves down to flick his tongue against her nipple. A sharp gasp sounds above him and Jackson smirks, sealing his lips around the hardened skin, sucking on it slowly.

When she tells him to go harder, Jackson hesitates for a moment before obeying. He pulls all the way out and thrusts into Stiles quickly, sucking on her nipple harder, worrying it between his teeth. Stiles moans loudly and grips his hair harder than before, her nails scratching against his scalp, causing Jackson to growl.

“Oh, fuck, Jackson.” Stiles’ voice is breathless and she moves her hips in time with Jackson’s, the pain she felt before not fading completely but by this point it’s just a dull ache. She actually kind of likes it and tights her legs around Jackson’s waist, urging him on. “Come on, Jacks — _fuck me_.”

Jackson groans and moves up, sucking on the juncture between Stiles’ neck and shoulder, biting the skin as he starts thrusting in harder. The sound of skin slapping against skin fills the air and gets drowned out only by the noises Stiles is making. The tiny whimpers, breathless moans, gasps, and soft cries she makes only has Jackson fucking her harder.

After a moment, Jackson straightens up, moving his hands down to Stiles’ hips, gripping them tightly as he pulls her down against him. “Fuck, you feel  _so_  fucking good,” he moans, opening his eyes to look down at her, biting his lower lip. Lifting a hand, Jackson cups Stiles’ breast and squeezes gently, rolling her nipple between his thumb and middle finger.

“Oh.  _Ohmygod_ , Jackson,” Stiles moans, her back arching as she moves a hand to her other breast, mimicking his actions. A shudder runs down her spine and she moves her free hand down, rubbing the pad of her middle finger against her clit. The sensations — the hands on her tits, the finger rubbing over the sensitive skin of her clit, and Jackson’s cock slamming inside of her — is almost too much for Stiles to handle and she gasps his name loudly.

“Yeah,” he answers, his voice rough and breathless, “come for me.” 

Stiles’ chest rises and falls with her harsh breathing, her breast moving against Jackson’s hand as he continues to squeeze and play with her nipple. He pinches it hard, sensing that Stiles is getting closer to coming from the way she smells and the way her walls clamp down around his shaft.

All it takes for Stiles to come is Jackson’s hips snapping violently against hers, his fingers pinching her nipple again, and her finger to press hard against her clit. She’s coming then, her back arching and her body trembling, Jackson’s name falling from her lips in a loud moan, the sound tapering off into a whimper. 

“Fuck, Stiles. That’s it, baby, come,” Jackson whispers, stilling his hips for a second before thrusting into her slowly. He can feel how tight she is, her muscles clenching around him and relaxing, only to clench again. 

Whimpering loudly, Stiles drops her hands away from her body, a thin sheen of sweat covering her skin. She’s sated and completely blissed out, a lazy grin settling on her face until Jackson starts thrusting into her harder. Biting back a scream, she tips her head back and continues to move her hips against his, her body buzzing from the over stimulation.

Stiles licks her lips and moves shaky hands to Jackson’s chest, dragging them down slowly, digging her fingertips against his abs. “Come for me,” she rasps and moans, lifting her hips to rotate them slowly, her legs falling away from his waist. 

“Talk to me.” The words come out in a soft, raspy whisper and Stiles hums, dragging her hand up to press a finger against Jackson’s nipple. She rubs the already hard nub slowly, opening her eyes to look up at him. “Fuck — or do… do that.”

“You like when I play with your nipples?” Stiles asks quietly, moving her other hand up and pressing her thumb against Jackson’s other nipple, rubbing them both slowly. “Fuck, Jackson, you feel so good inside me. So big.”

Jackson groans and continues thrusting into hard, his hand settling on her stomach, gently pushing Stiles onto the bed. He slams into her, his head back, spine bowed, and hands wrapped tightly around Stiles’ hips. One more rough thrust, combined with Stiles pinching his nipples, and Jackson is coming, nearly howling her name as he does.

His hips still against her, body twitching and shoulders trembling as he leans over Stiles, his breath coming out in harsh pants. A bead of sweat rolls down the bridge of his nose and Stiles wipes it away, pushing his short bangs away from his forehead with a smile.

“Holy shit..” Jackson laughs quietly and leans down, kissing Stiles slowly, moving a hand up to cup her cheek as he holds himself up with the other. When he pulls back, he rests his forehead against hers and breathes slowly, catching his breath before his sits up. 

Biting his lip, Jackson pulls out of Stiles and takes the condom off, tying it off before throwing it onto the floor. He smiles down at her and goes to pick his t-shirt and boxers off the floor, tugging the latter on as he heads back to the mattress. Without saying a word, Jackson hands Stiles his shirt and climbs back into bed with her, laying back as she sits up, pulling the fabric over her head.

Stiles sighs and lays back, turning over to face Jackson, curling up against his side. “That was… something,” she murmurs and laughs, humming when she feels him kiss the top of her head.

A few minutes pass and neither of them say anything; Jackson just listens to Stiles’ heartbeat and breathing, running his fingers through her hair. He kisses the top of her head again and moves his lips along her hairline.

“Are you alright?” Jackson asks, lips brushing along Stiles’ forehead as he speaks.

“Hmm.” Stiles wraps her arm around his waist and nods, chuckling. “I’m a little sore and tired but, other than that, I’m perfectly okay.” She pauses, chewing her lip. “Are you?”

Jackson nods and smiles, mumbling, “I’m good, Little Red.”

“Does that mean you’re going to be my Big Bad Wolf from now on or was this just a one time thing? Because, I mean, I’m okay with that — but I’d much rather you be mine.”

“Are you asking me out, Stilinski?”

Stiles jabs her finger against Jackson’s ribs and laughs when he yelps. “Yeah,” she answers and sighs, “I guess I am. What do you say, Jackson?”

“I say…” Jackson breathes, wrapping his arms around Stiles tightly, ducking down to kiss her lips and nip at the upper one, smirking as he pulls away. “That I’ll be your Big Bad Wolf any day of the week.”

A smile spreads across Stiles’ face and she nods, smiling as she snuggles against Jackson, laying her head on his chest, just above his heart. She takes a deep breath and closes her eyes, yawning quietly, brushing her thumb along Jackson’s side. Stiles dozes off just as a blanket is being laid over her body and she clings to the body next to her.


End file.
